17-Phenyl-18,19,20-trinor-cis-4,5-didehydro-PGA1 compounds

ABSTRACT

The disclosure includes novel compounds which differ from the known prostaglandins PGF 2 α, PGF 2 β, PGE 2 , PGA 2 , and PGB 2  in that the carbon-carbon double bond in the carboxyl-terminated chain of the novel compounds is in the 4,5-position rather than in the 5,6-position, and in that there is a phenyl or substituted phenyl group in the other chain of the novel compounds. These novel compounds are useful for a variety of pharmacological purposes, including abortion, labor induction, and reduction of gastric secretion.

The present application is a divisional application of Ser. No. 580,747,filed May 27, 1975, now issued as U.S. Pat. No. 4,032,561, on June 28,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,032,561, issued June 28, 1977.

I claim:
 1. An optically active compound of the formula: ##STR1## OR ARACEMIC FORM OF THAT COMPOUND AND THE ENANTIOMER THEREOF, WHEREIN R₁ ishydrogen or alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms,inclusive, phenyl, or phenyl substituted with one, 2, or 3 chloro oralkyl of one to 4 carbon atoms, inclusive;Wherein M is ##STR2## whereinR₂ is hydrogen, methyl, or ethyl; WHEREIN E is trans--CH=CH-- or --CH₂CH₂ --; wherein R₈ is hydrogen and R₉ is hydrogen, methyl, or fluoro, orwheren R₈ and R₉ are both methyl or both fluoro, with the proviso thatneither of R₈ and R₉ is methyl when R₂ is methyl or ethyl; Wherein C_(t)H_(2t) represents a valence bond or alkylene of one to 9 carbon atoms,inclusive, with one to 6 carbon atoms, inclusive, between --CR₈ R₉ --and the ring; and Wherein T is alkyl of one to 4 carbon atoms,inclusive, fluoro, chloro, trifluoromethyl, or --OR₃, wherein R₃ isalkyl of one to 4 carbon atoms, inclusive and wherein s is zero, one, 2,or 3 with the proviso that not more than 2 T's are other than alkyl;including alkanoates of 2 to 8 carbon atoms, inclusive, andpharmacologically acceptable salts thereof when R₁ is hydrogen.
 2. Anoptically active compound according to claim 1, wherein E istrans--CH=CH--, R₁ is hydrogen, methyl, or ethyl, M is ##STR3## s iszero or one, T when present is chloro, fluoro, or trifluoromethyl, R₈and R₉ are methyl, or R₈ is hydrogen and R₉ is fluoro, and C_(t) H_(2t)is --CH₂ -- or --CH₂ CH₂ --, and pharmacologically acceptable saltsthereof when R₁ is hydrogen.
 3. An optically active compound accordingto claim 1, wherein E is trans--CH=CH--, R₁ is hydrogen, methyl, orethyl, M is ##STR4## wherein R₂ is hydrogen or methyl, s is zero or one,T when present is chloro, fluoro, or trifluoromethyl, R₈ and R₉ arehydrogen, and C_(t) H_(2t) is --CH₂ -- or --CH₂ CH₂ --, andpharmacologically acceptable salts thereof when R₁ is hydrogen. 4.cis-4,5-Didehydro-17-phenyl-18,19,20-trinor-PGA₁, a compound accordingto claim 3, wherein R₁, R₂, R₈, and R₉ are hydrogen, s is zero, andC_(t) H_(2t) is --CH₂ --. 5.cis-4,5-Didehydro-17-phenyl-18,19,20-trinor-PGA₁, methyl ester, acompound according to claim 3, wherein R₁ is methyl, R₂, R₈, and R₉ arehydrogen, s is zero, and C_(t) H_(2t) is --CH₂ --. 6.cis-4,5-Didehydro-15-methyl-17-phenyl-18,19,20-trinor-PGA₁, a compoundaccording to claim 3, wherein R₁, R₈, and R₉ are hydrogen, R₂ is methyl,s is zero, and C_(t) H_(2t) is --CH₂ --. 7.cis-4,5-Didehydro-15-methyl-17-phenyl-18,19,20-trinor-PGA₁, methylester, a compound according to claim 3, wherein R₁ and R₂ are methyl, R₈and R₉ are hydrogen, s is zero, and C_(t) H_(2t) is --CH₂ --.